The Last Person He Expected
by littlecat1231
Summary: Sam's at a loss and has very little hope left. That's when she walked through the door... Part 1 of The Fly So High and Fall With Grace Series
1. Chapter 1

Sam sat at a table within the diner that was closest to his motel. A little run down thing with only one waitress and a cook running the place at any given time. The waitress, Sam never did get her name, was small women with light chestnut hair. She had kept side-eyeing Sam and giving him filtration smiles whenever their eyes met, but he only returned them with a smaller, polite smile with tired eyes before returning to the laptop and papers in front of him. It wasn't like she wasn't pretty or anything, in fact, Sam found her quite attractive and if he wanted to he would try and flirt right back, but, he just wasn't in the mood right now. He hadn't been for some time, all of his energy and effects had been focused on finding a way to get Dean and Cas back from… whatever they were. Hell, he didn't know if they were still alive.

Sam quickly banished that thought from his mind and return to the laptop, news articles blurring together. He couldn't afford to think like that. He had tried to summon Cas numerous times in that past couple of months in numerous different ways, but that hadn't worked. It was most likely that wherever Dean and Cas where they were stuck. He had even tired tracking spells for both of them, but, yet again, that had done nothing. His only real hope in all this was that wherever they were, that Dean and Cas were most likely together.

At this point, he was getting beyond dispute. He had already tried to summon a Crossroads Demon, several in fact, to see if he could try and get some information out of them if they had any. But there was no bite. All of the demons that he tried to contact seem to be nowhere around and wasn't that fucking bullshit. For the past seven years or so, demons couldn't seem to get enough of the Winchester Brothers. No matter which way they turn or how fast they drove, a mother fucking demon seemed to be around the corner. And now, when Sam needed one the most and wasn't that fucked up, they were nowhere to be seen.

Crowley was likely hiding far away from Sam. And shit, just the thought of Crowley made Sam even more depressed. Ever since his disappearing act with Kevin he had been trying to get information about him too. However, somewhat surprisingly, Demon activity had been at an all-time low as of lately. Sam was pretty sure that that was all Crowley's doing. He had also tried to summon Crowley several times, but again, there was no fruit for that labour. Kevin phone was also disconnected and tracking spell wasn't working him either.

Soon after he realised that he wasn't going to get anywhere with the demonic crowd, he quickly turns his attention to the Angelic flock.

He sat there for a moment when he realised that he had turned to Demons first before he turned to the Angels and took a second to look at his life from an outside perspective. Where he was less wary of Demons then he was of Angel. Even if it was only slightly. Very, very slightly.

The reason for this, of course, was that you could always trust a Demon to double-cross you the first chance that they got. Angels on the other hand... Well, they were either smart enough to feign innocent and peace until they got what they wanted or they were naive enough to believe in what they were told and took it for gospel. Even if they were in the wrong, the latter type of Angels wouldn't figure it out until it was too late.

But, the Angels were a bust too. For the most part, the Angels seem to be quiet quite too. No actions to restart the Apocalypse or any hint of a Civil War continuing. From what Sam could make out of it, they all just seemed... Lost. He hadn't been able to get in contact with that many Angels, but from the ones that he had, they all, for a lack of a better word, seemed really dejected. He had to admit that he did feel a little sorry for them. The little information that Sam could get out of them was that for the moment, they were just trying to figure out what they were going to do. Sam had slightly panicked at that, but after a belief talk, with Holy Oil by his side and a very visual Angel blade up his sleeve, they all assured him that they weren't going to try a bring the end of the world again, seeing as how that had turned out last time and that they were all tired of fighting each other, so there wasn't going to be another Civil War as far as they could tell. They, however, didn't have any information on Dean and Cas, though. One or two of the Angels that had been loyal to Castiel during the war, promised to look into it, but they hadn't been in contact since. Most other Angel seemed reluctant to help Castiel at all, considering what he did and all, with opening the gate to Purgatory, becoming the new God and murdering a load of their siblings. With the added bonus of letting one of God's deadly creations back into the world, even though he had helped to destroy them soon after. Sam could, begrudgingly, see their point.

Overall he was surprised that he wasn't on their shit lists. Okay, so maybe he was, but the Angels and Demons weren't doing anything about it, so that was surprising. He was pretty sure at this point that he and Dean were on multiple Angel and Demon shit lists with orders to "Kill on sight". But that didn't seem to the case. For the most part, they seem cautious even interacting with him.

Letting out a long-suffering sigh, his shoulder slouched and eyes half closed, he turned towards his coffee. It had more than likely gone cold by now and his salad looked like a pitiful pile by his side half eaten. The briefs of memories crossed his mind and he couldn't help but smile as he heard Dean complain about Sam's choice of food and "to keep that crap away from him" as he scoffed down a burger, or, as Dean had put it "Real food for real men, Sammy."

The smile vanished and was replaced with a grimace of the thoughts of what could be happening to his brother or Cas, his other brother in every way, apart from blood and no one could make him think otherwise. Okay, so he had made some mistakes, but so had he and Dean. But he always tried to make up for them and always protected him and Dean, even if he when about it in all the wrong ways and got hurt in the process.

Even after months of research and tracking across the country, he still had no idea about what had happened to Dean or Cas.

Sam ran a hand across his pale face, rubbing his thumb and forefinger against his eyes, tiring to rub some of the sleepiness away. In the hopes of gaining more energy he gulped down the disgusting tasting coffee, that he assumed would have tasted a lot nicer when it was hot, and proceeded to stare blankly down at the pieces of paper in front of him. All the coffee seemed to do was to sit heavily on his stomach.

He knew that going too long without sleep was dangerous, especially in his line of work. Lucifer had made that abundantly clear when he was in Sam's head, yet even with Cas taking away the hallucinations the nightmares of his time in The Cage and of his time as a Hunter still haunted him. Make sleeping for more than a few hours a night a scarce thing.

The diner wasn't very busy. The sun shown through the clear glass windows, reflecting off the recently wiped down surfaces. In one corner, there was an old couple sitting together and drinking coffee while doing a crossword puzzle; an old routine by the looks of it. Three tables down a family sat quietly, the parents obviously tired and their small children sat soundlessly while they were drawing on some paper. The quiet scratching of their pencils lessened the suffocating silence, but not by much.

Staring continuously at the laptop and getting nowhere, was starting to annoy Sam. Couple that with little sleep, particularly no food and the five cups of coffee that he had had in the past three alone was starting to give Sam a headache.

He was getting nowhere fast. Just like yesterday. And the day before that, and the day before that. Just like the last three fucking months. He was just about ready for chuck the laptop through the window and...

He did know how long he could continue like this.

In the back of his mind, he could hear the sound of the diner door opening and the bell on top of it give a little ring. The diner was quiet and peaceful, all things considering, so he didn't bother to look up and see who had walked in. He didn't really register that someone had walked in. His mind cloudy and head heavy. He just wanted to sleep. To sleep without the constant recurring nightmares of Dean trapped or dead. No way of Sam being able to save him. The nightmare of Cas laying on the floor blooded and broken. The burn marks of wings scorched out behind him.

The moment he realised that someone else had walked into the diner and that something was wrong, was the moment someone sat in the chair opposite to him. The person just slid into the booth without a word and calmly placed their forearms on the table, hands laid flat and folded in front of them.

Sam quickly tensed, his right hand steadily made its way to Ruby's knife, hidden safely in the fold of his jacket which was laying next to him.

He ran his eyes over the person, a woman, to assess the threat. For all intensive purposes, the woman sitting opposite to him seemed harmless. But then again, some of the most dangerous things that he had come across had looked purposely harmless. But as he looked closer let, kept his eyes trained on her, he could see there was something clearly... Off about this women. Sam couldn't put his finger on it because the harder he looked the more he noticed almost everything seemed off about her. The more he looked the more he wanted to look away. To look away and just ignore her. Ignore it?

The woman's hair was just too black, not dye but just, too dark. Like the light couldn't reflect off it. Her skin was pale also, the darkness of her hair making it more so, but it seemed to be... Glowing? It wasn't a pleasant, warm glow, but a hast, bright glow. Her eyes were crinkled at the edges because of her smiling and they just seemed too old of someone who looked that young. She appeared to be no older than her early twenties, but her eyes looked ancient. They reminded him of Castiel's eyes. Holding secrets of a long forgotten past. Eyes that had seen endless wars and countless lives. The smile was the one thing that took Sam a moment to realise what was wrong with it. It looked someone who didn't know what a smile was had tried to copy someone else's smile, but couldn't quite get it right.

He scanned the room to find that no one else was paying attention to the new arrival and were all content to carry on with what they were doing.

Turning his attention back to his unexpected guest and tightening his grip on the knife, a gun would bring too much attention if the situation turns bad, he waited for something to happen but, there were was nothing. She just sat there, smiling at him.

Finally, after an unspecified amount of time that seemed to drag on for an eternity, she said,

"Forgive me if I am wrong, but I do believe that we are to exchange pleasantries." Her voice soft, silk-like and the way she spoke made Sam think about the way that women would talk in the old western movie that he and Dean use to marathon with Bobby one their very rare days off. And wasn't that a kick to balls.

Sam just stared at her. Not knowing what to really do, he just replied with,

"Er, yeah."

She smiled a little wider and that just made Sam even more uncomfortable.

"Hello." She responded. Nothing more.

With another quick scan around the diner, he concluded that everything was still the same.

Narrow his eyes at the woman and straightening himself, pulling back his shoulders to make himself appear bigger, he gave a short and firm hello back.

The silence between them seems to be deafening.

"I do believe that I am making you uncomfortable, I apologise. Introducing myself would make you more at ease, correct?" At her inquiry, Sam nodded. The more information he could get out of her without revealing any himself would be a bonus.

The women straighten, looking down at herself as she ran her hand down top, a simple plain white t-shirt. Meeting his glaze again she placed her hands in her lap and cleared her throat.

"Well then." She stated. "Hello Samuel Winchester, I am Azrael."


	2. Chapter 2

A dozen or so thoughts passed through Sam's mind, the information that he had come across for someone or something with the name Azrael. There had been little information on Azrael and what he did find was all mixed up in different religious' and scriptures, so he didn't really know what right, what was made up and what had been gotten wrongly transcripted. One of the things that they all agreed upon though was they were, in one way or another, supposedly an Angel of Death and in Sam's case anything to do death, especially when Angels were involved, wasn't good by a long shot.

"Azrael huh?" Sam said in a tone that he hoped sounded likely indifference, but with his heart pounding in his ears he couldn't really tell. "What do ya want?" He asked.

Azrael tilted her head to the side, the same way that Cas did when Dean made a reference to something he didn't get. Sam grip on the knife didn't loosen up one bit.

"I thought that introductions would make you more at ease, but perhaps I was wrong." Her voice was still the same, the silky smoothness that made Sam want to relax.

"Stop that." He snared. He didn't really want to get in a fight with Angel, in a public place for that matter with civilians around them, but he would gank her if necessary.

She looked taken aback by Sam outburst, pushing herself back against the booth. She did a quick check of herself, hands patting against her body as to try and see what he was talking about.

"I beg your pardon but stop what exactly?" She asked slowly. "I haven't taken a form like this in many years," she emphasised her point by extending her arm out in front of her and flexing her fingers."So you'll have to tell me if I have gotten anything wrong. Humans have changed a lot over the past couple of millennia." The confusion that mirrored her face almost made Sam believe that that was the truth.

If he was perfectly honest with himself, there was a small bit of him that wanted to believe that she was telling the truth. Usually, with these types of people, he and Dean got a sense of when something was wrong and he wasn't getting it with this one. However, Sam was always the more trusting of the two; Dean had pointed that out many times before and always belittle him about it. Telling him that it was going to get him killed. But after Ruby and with Dean no longer by his side, he had decided to put his optimism in people away for the moment. Just until he got Dean and Cas back. Then they could go back to the way things were.

Sam scowled at her.

"The thing you're doing with your voice." He told her bluntly. Better to play dumb and see what your enemy was up to, thinking that they had the upper hand, when in reality they always relieved a little too much information, thinking that Sam and Dean didn't understand what they were saying. Or hell, sometimes even Cas would play this game and win. Because when people thought that you weren't paying attention, that when it was the best time to strike. He smiles inwardly at himself at the thought of Cas outsmarting his opponent by playing dumb, something that Sam like to think the little guy had learned from them. Cas was an honorary Winchester through-and-through.

The confusing on Azrael's face bled into surprise and understanding.

"Oh!" She exclaimed. "I forgot about that. I am sorry." The sincerely in her voice could've been real, but Sam wasn't fully buying it. "If you'll give me one moment." She took a deep breath, and the lumination around her disappeared. Now she seemed more normal, more human. "Is this better?" She questioned. She had loss the silky tone and Sam didn't feel the effects of calmness anymore. Sam nodded stiffly.

"I guess you aren't one for small talk and want to get down to business." Sam raised his eyebrows at that but didn't say anything.

She looked straight into Sam's eyes like she was boring right into his soul and that made him flinch. "I'm going to get Castiel back, and I need your help."

Now, this can go either way. Azrael could be a Castiel loyalist and want him back to lead the Angels in whatever revolution she has in mind, possibly starting another Civil War in the process. Or she could want the exact opposite and want to kill Cas for all that he has done. Either option wasn't favourable in Sam opinion, but alive Castiel was slightly better.

"Why should I help you?" He asked. "For all, I know you want to find Cas to kill him, and no way in hell am I going to help you do that." He kept his voice firm. Not giving her an inch.

The look of shock, hurt and confusing passed across her face as if she could quite believe what had come out of his mouth. If she was acting, she was one of the best Angels that Sam had ever seen.

Twisting her face into an expression of distant, her jaw set tight, she lends forward,

"I assure you, Sam Winchester, from now on if anyone dares lay a hand on Castiel, they will find themselves staring up at the wrath of Death." Azrael left no room argument. Her tone thunderous.

"So it's true, you are the Angel of Death." Sam declared.

Azrael seemed to relax at the change of the subject, falling back to rest in her seat. She seemed to ponder the statement for a moment.

"I'm some ways I suppose, yes." She started, taking a second to choose her next words carefully. "But I'm not like the Reapers or Death himself, I'm more, behind the scenes."

Sam frowned deepened.

"Meaning what exactly?" He questioned bluntly. Azrael started to look uncomfortable.

"I," she cleared her throat, "I dealt with the Reapers and their problems…"

"What kind of problems?" Sam asked curiously and causally. Azrael pursed her lips.

"Any that they have with each other, problems other creatures interfering with their work. On several occasions, I've dealt with a Reaper gone rogue." She scowled.

"Rogue Reaper?" Sam deadpanned.

Azrael signed and pinched her face in such a way that meant she didn't really want to talk about it. Tough, Sam thought. He didn't trust her, and any creature with the word 'Death' in their name or description just ending up being bad news. He knew that much.

"Reapers that have gone rogue in the past have either taken the souls for their own personal gain, while others have made deals with Demons for certain souls that should have gone to Heaven, but the Demon wants it for themselves for whatever reason. I make sure to deal with all parties involved and the souls go to the right locations." She looked strain while talking about it, but Sam wasn't going to stop pushing. If this was true than Reapers would have to go on 'The List' of creatures that should be looked out for.

Creatures on 'The List' were usually ones that had to be killed on sight or watched out for in case they did anything dangerous and needed to be stopped.

Also, Sam wasn't quite sure what she meant when she said 'Deal with all parties', but it didn't sound good.

"What do you mean by 'deal with'?" He questioned firmly. Azrael just gave him an irritated glare.

"I made sure that they were fairly and justly punished for their actions," she spoke slowly as if speaking to a child. "Don't get me wrong Samuel, I am not like my Brothers and Sisters, I do not like spill blood, in fact, I have personally only killed three being in my lifetime and I am not proud of doing so." Then she took a deep breath. "Despite my title, I don't partake in taking the life of others." Her face shifted into an expression of sorrow. "I have come to you because we need each other's help. I do not know where to start looking for Castiel or for your brother, but I can help you find what we need to find them and I am willing to help you to make that happen."

Azrael leaned forward in her seat and looked Sam straight in the eye. "I believe you Humans have a saying,'Two head are better than one.' Yes? And I believe that means that working with another person and using all their combined knowledge while working together, is better than trying to figure this all out on your own."

Sam allowed himself to shift slightly, his mind going a mile a minute, working out all the ways that this could go possibly wrong. She could easily be setting a trap for him, some people would absolutely love the idea of having all the Winchesters dead or incapacitated. She could possibly still want Cas dead, playing Sam so that she could be hundred percent sure that Cas was dead already and if not finish the job herself. This could even all be a ploy to distract him from some other plot that the Angels didn't want him to know about.

On the other hand, Sam was at his wit's end. For the past several months with no leads and no sign of Dean or Cas anywhere, he was just about desperate enough to expect her help. He could pick her brain for knowledge about the Leviathan and what was truly going on with the Angels. She could maybe even help him find Kevin.

Sam took a breath and searched Azrael's face, trying to get a better read from her. Angels were usually an open book; emotions, the ones that they did have, either confusion or contentment, were shown clearly. But if she was really was trying to manipulate him, this could all easily be an act.

As Sam's shoulders slouched a little, a bit of tense easing away. Azrael smiled.

"Now," she announced confidently. "Are we going to do this, or what?"


End file.
